betulin 3β-O-α-L-arabinofuranoside | 1049318-99-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: betulin 3β-O-α-L-arabinofuranoside
• 英文别名: (2R,3R,4R,5S)-2-[[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-yl]oxy]-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 1049318-99-1
• 化学式: C₃₅H₅₈O₆
• 分子量: 574.842
• InChiKey: XHMWRLRVPGXYEG-XIZQDZLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  41
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  28-O-tert-butyldiphenylsilylbetulin 3β-O-α-L-arabinofuranoside 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 以37%的产率得到betulin 3β-O-α-L-arabinofuranoside
  参考文献：
  名称：

  Synthesis of two natural betulinic acid saponins containing α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranose and their analogues

  摘要：

  A concise synthesis of naturally occurring betulinic acid saponins bearing an alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranoside moiety at the C-3 position is described. Betulinic acid 3 beta-O-alpha-L-rhamnopyranosyl-(1 -> 2)-[ -D-glucopyranosyl-(1 -> 4)]-alpha-L-arabinopyranoside isolated from Pulsatilla koreana and 28-O-beta-D-glucopyranosyl betulinic acid 3 beta-O-alpha-L-rhamnopyranosyl-(1 -> 2)-a-L-arabinopyranoside isolated from Schefflera rotundifolia were easily synthesized for the first time using a stepwise glycosidation approach. The overall syntheses involved eight linear steps starting from allyl betulinate and commercially available L-arabinose, L-rhamnose and D-glucose. The syntheses of betulin and betulinic acid O-glycoside analogues containing an alpha-L-arabinose moiety are also reported. These results open the way to the synthesis of various lupane-type saponin derivatives as potentially bioactive compounds. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.029

文献信息

• Synthesis of two natural betulinic acid saponins containing α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranose and their analogues
  作者：Charles Gauthier、Jean Legault、Serge Lavoie、Simon Rondeau、Samuel Tremblay、André Pichette

  DOI：10.1016/j.tet.2008.05.029

  日期：2008.7

  A concise synthesis of naturally occurring betulinic acid saponins bearing an alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranoside moiety at the C-3 position is described. Betulinic acid 3 beta-O-alpha-L-rhamnopyranosyl-(1 -> 2)-[ -D-glucopyranosyl-(1 -> 4)]-alpha-L-arabinopyranoside isolated from Pulsatilla koreana and 28-O-beta-D-glucopyranosyl betulinic acid 3 beta-O-alpha-L-rhamnopyranosyl-(1 -> 2)-a-L-arabinopyranoside isolated from Schefflera rotundifolia were easily synthesized for the first time using a stepwise glycosidation approach. The overall syntheses involved eight linear steps starting from allyl betulinate and commercially available L-arabinose, L-rhamnose and D-glucose. The syntheses of betulin and betulinic acid O-glycoside analogues containing an alpha-L-arabinose moiety are also reported. These results open the way to the synthesis of various lupane-type saponin derivatives as potentially bioactive compounds. (c) 2008 Elsevier Ltd. All rights reserved.